Q: I've heard of people giving gifts to everyone from their neighbors to their postal carriers and hairdressers, is that expected?
A: The bad news is that most peripheral holiday gift-giving falls into a vast gray area in which there are few easy answers; the good news is that you can make your own decisions based on the depth of your relationships. You would likely give something to a daily caregiver, for example—but the guy who skims the pool? Your call. Likewise, the neighbors: feel free to give them home-baked cookies, a card, or a hearty holiday greeting.
For regular service providers, a five- or ten-dollar café gift card makes a handy all-purpose holiday “thank you”—but beware that the U.S. postal service has strict rules about what you can and can’t give a mail carrier (no cash; no gift worth more than $20). Remember: You’re expressing thanks, not “buying” good service. (That said, though, last year we forgot a gift for our newspaper delivery person, and our daily Times migrated from the doorstep to somewhere deep under the car. This year: fruitcake!)
— Catherine Newman